Wayne and Cain: Winged Creatures
by Master of Chronicles
Summary: 18 year old Damian Wayne has been left in charge of protecting Gotham and wants former assassin Cassandra Cain to be his partner...in every sense of the word. Will she accept? Romance as a vigilante in the city of crime isn't easy, especially when villains keep trying to kill them at every turn. (Damian/Cassie) Involves most of the Bat Family.
1. Superman Saved Them

**I've had this bouncing around on my computer for several years now, the idea being pre New 52. This doesn't follow any sort of canon per say, but does try to keep true to the characters. I always thought that Damian and Cassandra would have an interesting chemistry between them. Damian tackling ideas like romance and real love seems very funny to me and I wanted to play around with that idea.**

 **Note: Dick Grayson and Barbara Gordon are my favorite DC couple. Not important, just wanted to share.**

 **DC owns these characters, but if I could make money from them, I would.**

* * *

Superman saved Them

Damian stood still as a statue directly in the center of the training room of the dark Batcave. The matted floor felt cool against the soles of his bare feet as he closed his eyes and concentrated. When he was a boy, Damian had been taught that the best teacher was the mind. The mind could conceive any challenge, any scenario, any condition to be overcome. And Damian had spent years learning to master his mind.

In his hands was his sword; a rare, straight edge katana uniquely made for him. It was sheathed inside its polished, black polystyrene scabbard, ready and waiting for its master. Damian, with the patience and discipline of his training, mentally envisioned an ancient dojo built in the darkest shadows of the Himalayas, the wood beam floor stained with spots of dried blood from many aspiring students. Damian then created four foes from figment, giving each opponent size, weight, experience and skill. He armed them well, with exotic weapons from the deadliest corners of the martial art world. He also gave them a lusting for his death.

Now, Damian was ready to train.

The first assassin, armed with Dao blades, attacked first. Damian's sword flashed as he drew it with his right hand and slew the attacker in one strike. But he wasn't fast enough to have stopped the man from slicing an inch long gash just above Damian's left eye. The resulting imaginary blood began to blind him.

Two other assassins carrying spears came at him and he quickly countered their flurry of blows. The sheath in his left hand became both shield and club, deflecting blows as well as giving them. One man got the sword through his eye, the other was cleaved cleanly in two from the waist.

Only one last fighter remained.

But this one was special. This assassin hadn't attacked while the others were alive. He had waited patiently, watching the young Wayne as he fought, looking for weaknesses. He was immense, as imposing as Bane with the cunning of Batman. He was Damian's greatest fear.

Damian held his blade in an expert position of defense, keeping his eyes firmly locked on his self-created challenge. He knew it wasn't real, that he wasn't really in Asia fighting for him life, about to dance with an opponent he had lost to many, many times. But in that moment, as real sweat ran down his face and his lungs burned with the effort, Damian _chose_ to believe he was facing reality.

The final assassin moved first, forcing Damian to leap back and counterattack before it was too-

"Sword training again, master Damian?" the intrusive voice of Alfred Pennyworth shattered Damian's battle meditation, the older English man carrying a pitcher of water and a hand towel. "Killing yet more members of the league of Shadows, I imagine."

"I was." Damian muttered with barely restrained frustration.

"I thought you and master Bruce had reached an agreement that you would no longer use lethal force."

Damian sheathed his sword with a snap, walking off the training mat and over to the pitcher of water and hand-towel that awaited him in the butler's hands. In his mind Damian was killing, but the old man didn't need to know that. "It's possible to use a sword without killing anyone, I would have you know."

"I fenced in my younger days, Master Damian. The sword is used solely for killing." Lectured the Englishman as he waited patiently for the young Wayne to finish drinking.

"So is most martial arts." Damian countered. "But my father has mastered each so precisely that he can use every style known to man, and even a few he has invented himself, and be entirely non-lethal. I intend to do the same with the sword."

"So those imaginary enemies you just fended off all survived?"

Damian growled beneath his breath. He should have never explained to this walking fossil his training techniques. Damian then grinned wickedly. "Actually they did. Superman saved them. He showed up at the last second and stitched them all back up at the molecular level. Even the one with the split brain."

"I'm sure he did." Alfred sighed, "Even at his worst, master Bruce has never been as _terrifying_ as you. I wonder how on earth you intend on...umm...shall we say... _convincing_ Ms. Cain to accept your proposal of joining forces to defend Gotham in Batman's absence. I very much doubt she'll be looking forward to your bloodbaths night after night."

"I haven't killed in four years, Pennyworth. And I haven't maimed...much...in three." Damian reminded the butler as he stripped off his skintight training armor and hung his blade on a rack next to his other swords and headed for the showers. "Besides, I don't believe we will need to patrol together _every_ night."

"What a relief." Alfred added dryly.

Damian had just stepped into a stall and turned the hot water on when...

"ALERT! ALERT! ALERT!" The Cave's supercomputer blared nosily as red lights flashed.

"It better not be Blue Beetle asking for help again..."

"Master Damian." Alfred had already reached the monitors, reading and listening to the emergency lines and police reports. "It seems someone was foolhardy enough to attack Iceberg Lounge during a rather special ceremony."

"You mean Cobblepot's place?" Damian laughed as the water doused him clean. "So who's getting the medal of valor?"

"Unknown. But they have taken hostages."

"Ha!"

"Including the owner himself."

"So Penguin is going to get iced. What of it? Sounds like he only getting what he deserves."

"Your lack of concern for the lives of others aside, I would normally be inclined to agree..."

"But?"

"I'm afraid the event that was taking place was for Mayor Hamilton Hill's reelection. Most of the hostages aren't crooks."

Rolling his eyes, Damian killed the shower and, dripping wet, walked naked across the length of the cave as he headed to get his gear. "The timing is uncanny."

"Shall I cancel your dinner at the White Raven, sir? I'm sure Ms. Cain will understand."

"No." Damian said as he dressed in his newly modified Robin attire. Gone were the iconic reds and greens. His new costume was made up of black and grey kevlar armor, brass-knuckled gauntlets, steel toed boots, a white cape and hood with a large white "R" on his left breast. "I'll have this mopped up in a few hours. Just push the reservation from 7 O'clock to 9."

"Erm...sir? This is the White Raven. Even Master Bruce rarely ever gets a reservation. To reschedule is entirely unheard of."

"The restaurant is built on the top floor of Gotham Memorial High Tower, correct?"

"Yes..." Alfred didn't want to even guess at what the young man had in mind.

"Then tell them that I'll buy the rest of the building beneath them if they don't reschedule and convert it into the new Arkham Asylum. We'll see how well business is for them then." Damian said as he mounted his motorcycle and sped out of the cave into the late afternoon.

Alfred sighed. "Ah yes, money and threats. The Waynes' answer to everything."

* * *

 **As much I as wanted to just throw the story right into the Romeo and Juliette stuff, I needed to do a bit of world building first. This will be a story with as much Batman stuff as I can do, so it won't be just fluffy stuff. There will be punches, kicks, torture, crimes and bloody murder, with the occasional kiss.**

 **See you all next time!**


	2. Not Bad For A Rookie

**Hello! Thanks for the reviews and I hope you continue to enjoy the story! Let's get to it!**

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Not Bad...For A Rookie

The Iceberg Lounge boasted Gotham's newest Grand Hotel Casino, with the best games, fast food and faster girls in the city. Well over sixty stories high, it was lit by almost a hundred spotlights to give the appearance of an upright tower of crystal, a shard of diamond on Gotham's horizon reaching for the heavens.

To Damian, it was the cleanest looking cesspool in history. The sun had nearly set as he drove at dizzying speeds across one of the city's many bridges, weaving his motorbike expertly through traffic and pedestrians. It took him twenty minutes to reach the Iceberg, which had been sectioned off by the GCPD with countless squad cars and swat vans. The arrival of a costumed vigilante was so common that the men and women in uniform did not question him as Robin made a beeline for the commissioner.

"Have there been any demands?" Damian asked, the one question he had been trained to ask by his father. Demands hinted at motivation. Motivation hinted at a criminal's state of mind and how best to predict and defeat him.

Gordon blinked at the teenager for a moment. "Where's the big guy?"

"Doing big things." Damian threw back. "Are they asking for anything?"

"Yes. Money."

"Of course. Have they opened a dialogue?"

"Yes. But not with us." The commissioner added.

"What do you mean?"

Instead of answering, Gordon jerked his thumb upwards to a spot on the building nearly thirteen stories up. Damian made out several large broken windows side by side. Two thugs in samurai kabuki masks with generic semi-automatic guns stood watch. Then three more men showed up, dressed like the others, but holding what looked to be a large white log between the three of them. Damian gave a whistle when the men threw their load out the window, revealed it to be a canvas on which was written, "Nelsons, call 236-453-8495 for ransom payment."

"Impressive." Robin smirked. "Instead of negotiating with you, they're contacting the relatives of the hostages using the media. Give them a number to call and tell them where to wire the money, presumably untraceable offshore accounts. I assume they're actually releasing the hostages?"

"Yep. When the first hostage was released, everyone gave up on us handling the situation and followed suit." Gordon sighed, seeing a young woman and an older man leaving the Iceberg by the main entrance, running away from their captors as fast as they could. Several of Gordon's men and women wrapped them in blankets and took them to their families. "If we try to call instead of the families, the hostage dies. They made that _very_ clear. This is happening all around the building and things are going rather smoothly. If this continues, most of the hostages will be safe."

"Nothing for Cobblepot yet." Robin observed. "I doubt even his lawyers would spend his own money to save him."

Gordon smiled ironically at that statement. "Not even his mother would pay for his freedom, the scumbag."

"Well, I guess this will handle itself easily enough. I'll be going." Robin said, seeing no point in remaining. Besides, he had an appointment with...

"Not just yet." The commissioner interjected. "I want you to wait."

"Why?"

"They can't trade out all the hostages, otherwise we'll be able to storm them. They will have to keep a few for protection and have an escape plan. That means a potential for something to go wrong. I would rather have you around just in case."

"...Fine." Robin said, walking back into the nearest alley way. "If you want to reach me I'll be on the higher frequency end of your radios."

"Where are you going?" Gordon called out before the coming night swallowed the young man. "I thought you agreed to wait."

"I did." Robin called back just before disappearing entirely. "But I never said I would wait out here."

Damian's plan was simple. With the sun now below the horizon and Gotham in the early hours of night, the young man found the nearest building a few stories taller than the Iceberg Lounge five blocks away and accessed the roof.

Using night vision binoculars, Damian scouted the rooftop of the Lounge and saw it was guarded by five armed snipers, each in full tactical gear and several rocket-launchers. If a helicopter tried to land, they would blow it away. But Robin could glide in unseen until he was on top of them.

"It's a good plan." Said a feminine voice behind Damian, causing him to turn his head.

Cassandra Cain, known publicly as a former Batgirl, now Black Bat, stepped out of the darkness from behind a large roof vent and into the moonlight. Dressed in full body gear with a mask over her face, the young Chinese woman looked fully capable of taking down an entire crime syndicate.

Black Bat continued, "Find a safe spot to gather intel and form a plan of action. Smart. Just how Batman trained us to think."

"I apologize about dinner. I hope to resolve this as quickly as possible." Damian returned to his scouting, unfazed from Cassandra's sudden appearance.

"This is more important. Lives are at stake." Black Bat said understandingly. "Besides, you knew as well as I that keeping arrangements as members of The Family is very difficult. And since we are going to be together later on anyway, I figured I'd come and help."

Robin grinned. "So you guessed at my plan and knew what rooftop I'd be staging my attack from and waited for me? That's impressive. It only reinforces my belief that you are the right one."

"Right one for what?" Cassandra asked as she leaned next to Damian to get a look at the layout herself.

The young man brushed the question aside. "Later. Right now we take care of these goons. I suppose if you deduced my plan so far you've guessed the rest?"

"More or less." Black Bat replied. "Head for the roof, take out the snipers, infiltrate the Lounge and save the hostages after cutting off any means of escape."

A satisfied grinned crossed Damian's lips. "Not bad...for a rookie."

"Excuse me?" Cassandra's asked, surprise in her tone. "Didn't I beat you in a one on one fight before?"

"Sure, when I was a snot-nosed twelve year old. And fighting skill has nothing to do with this. As great as you are at punching, the plan you just laid out would result in the death of at least half the hostages."

"How?" pausing for a moment, Cassandra took a moment to use her imagination to play out the events of the plan she had just suggested. "If we took out the roof baddies, who are doubtless constantly reporting in to the others inside, their sudden silence would get noticed. The criminals would know something was up."

"Exactly." Damian nodded. "So with that in mind, what should we do?"

"...Break in where there are sure to be less guards. Somewhere in the middle of the Lounge."

"Very good. I assume your gloves have the window adhesion upgrade?"

"Of course."

"Then let's go."

Both heroes leapt off the skyscraper and opened their capes, gliding under the cover of darkness toward the Iceberg Lounge.

It took them three minutes of gliding to reach the target building, cut a hole in a window on the 22nd floor and slip inside undetected. The room Robin and Black Bat found themselves in was best described as an upscale hotel suit, complete with open bar and...many other distractions.

"A dancing pole?" Cassandra noted as they made their way to the entrance. "I guess Cobblepot does his best to keep his 'guests' happy."

"What better way to have a mobster agree to fork over a multi-million dollar investment than to hypnotize him with a few pretty girls? Girls that are often abused and beaten, addicted to drugs and kept in line by making an example of those who try to leave." Damian noted darkly as he cracked the door open.

The hall was empty.

"With snipers on the roof and most of the crooks on the lower floor watching the hostages and giving directions for the ransoms, a small skeleton crew will be patrolling the other floors." Robin eye's caught sight of a swiveling security camera down the hallway. "We need to get to the security room. That's where most of their eyes will be and where we can read the terrain the best."

"Which floor is it on?" Cassandra asked. "I don't have access to the Bat-Computer anymore. I haven't seen the blueprints."

"I have, on the drive over. It's three doors down on the right. We didn't break in on this floor for nothing."

Suddenly, through the open window behind them, both vigilantes heard a loud gunshot from further below their floor.

"Something tells me we need to hurry." Cassandra said evenly.

" _-zzzt- Robin, do you read me?"_ Gordon's voice cracked over Damian's earpiece.

"What happened?" Robin asked.

" _Punks just shot a young woman in full display to everybody because her lawyers tried to negotiate the ransom. -zzztttt- A lot more people are going to die very soon!"_

"On it. Hang tight." Robin looked at Black Bat, who nodded.

Both looked back toward the camera, waiting until it faced away, then made their move. Quiet as air, they sped down the hall, made it three doors down and rushed inside. Three armed men, dressed in clean suits and kabuki masks, with assault rifles in their hands, had only enough time to gasp in shock before getting attacked.

Black Bat jumped forward and kicked the nearest one so hard in the face she snapped the mask in half, revealing a broken nose. Still in the air, she threw a batarang at a second goon had been sitting in front of the dozen security monitors and had tried to sound the alarm over the radio. The batarang collided with his head with enough force to knock him out cold. The first goon tried to throw a punch, nose bleeding all over his suit, but got kicked in the teeth for his trouble. A quick choke hold finished him off.

Robin took the last and largest man. His straight edge katana sliced through the air as he drew it, cleaving the masked man's rifle neatly in two. Staggering back in surprise, the man was too slow to avoid Robin's heel, which struck him in the temple and sent him crashing unceremoniously to the ground.

"That's two for me." Cassandra said with a hint of pride.

"Night's not over yet." Sheathing his blade, Damian pushed the unconscious man that had been viewing the many monitors out of the chair and sat down, looking at the live feeds. "We got twelve men at the bottom floor with the hostages near the south elevators. Six are on the 13th floor, giving the ransom demands and...that's strange..."

"What?" Cassandra asked as she removed the kabuki masks from the other motionless goons.

"The basement cameras have been disabled." Damian observed, the three monitors for that section of the Lounge showing nothing but gray static."

"I thought the masks were just for show." Cassandra began, looking at the face of the man whose mask she broke. "But they are Japanese. Did Cobblepot make some enemies with the Yakuza?"

"No idea." Damian admitted. "I think...-tt-..."

"What?"

"Someone else didn't pay the ransom. They're taking a couple into the elevators at gunpoint and bringing them up to the 13th floor."

"We need to stop them." Cassandra said firmly.

"The moment we do they will open fire on the other hostages." Damian pointed out.

"We split up. I take the 13th, you take the main floor." Black Bat hurried out the door before Robin could reply.

"I love it when she takes charge." Damian grinned. Turning back to the monitor, his eyes narrowed at the three blank screen of what should have been basement surveillance. What was happening down there? "No time for that now."

He needed to get to the party floor fast before Gotham had it's biggest 1% massacre since his murdered grandparents.

* * *

 **Damian is one of those characters I never knew we were going to see in the Batman franchise. Back when Jason Todd came along they tried to have him talk back to Batman so that he would look tough. It didn't work so well in the long run with the fans. But Damian had this completely different mentality of trying to please his father while bashing all the other former robins with his fists. He was a robin Batman would have to thaw out, which makes for a really interesting read.  
**

 **And he made the perfect Robin for Dick Grayson's more light-hearted Batman.**


	3. Turkey And Dirty Money

**Truth be told I won't even be 100% happy with this chapter. I guess it's my lack of police experience that just makes me feel I've missed some very key details. I give mad respect to writers who know how to write this genre because it is not easy. You never want anyone coming off looking like an idiot. Plus, trying to write a Gotham story in a form that isn't movie or comic has it's own challenges. But blah blah blah, on with the tale!**

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Turkey and Dirty Money

For Cassandra, every life she saved was another excuse to convince herself she wasn't the monster her father had raised her to be. Even though she couldn't feel emotions the same way normal people would and didn't have enough humor in her to laugh at any of Dick Grayson's jokes, the persistent bitterness of guilt in her stomach was enough to drive her forwards.

Leaving the security room, Cassandra ran back to the room she and Robin had used to infiltrate the Iceberg Lounge and dove headfirst out the open window. The cold night rushed by like wind as she opened her cape to glide around the building in a downward spiral, hidden in the darkness, avoiding the spotlights from the police on the ground.

 _I have to think fast!_ She told herself. _Remember on what floor the hostiles are and what I must do to stop them before they execute that couple._

Recalling the image of the armed kidnappers holding a canvas with a phone number written on it out an open window, Cassie built a plan of attack. They were on the 13th floor, south-east side of the building using the south windows to show the canvas to the media below. In order to flank them she would have to come through the windows on the eastern side. She remembered seeing assault rifles, so taking out their guns had to be her first move.

 _Too late to come up with anything else._ She thought as she made a final loop around the building, already having chosen point of entry. _Time to go to work._

Black Bat startled the hostiles as she smashed through the windows, showering the room with shattered glass, buying herself a few precious seconds to act before they did. First came the flash grenade, which she tossed up in the air as it exploded.

"Agh! My eyes!" One man screamed.

"Shoot! Now!" Yelled someone else, firing wildly.

Dodging the best she could, Cassandra wasted no time throwing multiple batarangs into whatever hand held a gun. Cassandra hated guns. Each man's weapon clattered to the floor, giving her a few more seconds to take the advantage.

Having been trained to kill before getting her adult teeth, Cassandra could read the human body like a book. Muscle movements were like e-mails to her, telling her exactly what her opponent was going to do. The six men surrounding her were no different.

Aiming primarily at knees and elbows, Black Bat fought in one long, fluid movement. The men were dazed and confused, and when they did fight back it was sloppy and with very little technique. Whenever one tried to reclaim his gun she would break his hand. One went for a diving tackle, which she avoided by bending over backwards and watching him smash his own face into the wall.

She was just about done when two other criminals with the aforementioned doomed hostage couple walked in the room.

"What the-?!" The first goon cried out.

Dashing forward, Cassandra interrupted him with a disabling kick to the throat.

The second reacted faster, firing off a shot which she avoided by spinning in place. Sadly the stray bullet hit one of his friends who was trying to stand, killing the man instantaneously. Black Bat rushed the murderer, striking at his solar plexus to bend him in half and then finished him off with a knee to the face.

Making a quick scan, Black Bat saw the other hostiles were either unconscious or too hurt to be a threat any longer.

"Y-you saved our lives!" The young male hostage said as a woman twice his age clung desperately to his arm as they huddled in a corner of the room. Judging by how she was dressed, she wasn't his mother.

"Find an empty room and barricade yourselves in until this is over." Black Bat told them as she began restraining the goons with black zip ties.

Nodding, the couple slowly made their way to the door. The young man began to bend over to pick up one of the assault rifles.

"Don't touch that." Black Bat ordered. "Leave."

"But-" the young man began.

"Now!" She cried viciously, scaring them.

They sped off, almost tripping over each other. Cassandra looked out the broken window to the flashing red and blue lights of the countless police vehicles below with spotlights aimed at her location.

"Are you there, Commissioner Gordon?" She spoke into the headpiece built into her cowl.

" _Who the hell is this?"_ The man said in surprise.

"You knew me as Batgirl once." She answered.

" _...That doesn't narrow it down._ " He replied blankly.

"I'm the one that didn't talk."

" _Oh...right. Did you just attack those guys on the 13th floor? We heard gunshots. We thought something had gone wrong."_

"They were about to execute more civilians. But all hostiles have been dealt with. One fatality by friendly fire, I'm afraid. Robin should be mounting his assault on the main floor any minute. Be ready to move in at our signal." Black Bat began heading for the stairs.

" _Am I to assume the signal will be a big explosion or something?_ " It seemed Gordon had been around this block before.

"Hopefully not. Black Bat out."

Entering the stairwell, Cassandra looked over the railing to see the staircase spiraling down a dozen stories with enough room in the center allowing her to jump all the way to the bottom. Opening her cape to soften her landing, Cassandra pulled out two black, collapsible batons, ready to fight. She approached the door and peeked through the glass opening. The room was full of very dense smoke and only the red emergency lights were on. All was quiet.

Upon opening the door Cassandra realized why.

She found most the hostages laying motionless on the ground surrounded by a thick haze in the air, every last one bound and gagged. She approached the closest one, a woman around 30 in a blue dress and check for a pulse. She had one.

 _Must be some sort of nerve gas. Lucky I have a filter built into the cowl. Did Robin do this?_ Cassandra wondered. _And if he did, where are the hostiles?_

Her answer came as three of them jumped her out of nowhere, materializing from the smoke with brandished katanas, the red glow of the emergency lights giving their kabuki masks a very sinister appearance. They also wore gas filters, which meant it was them, not Robin, that released the nerve agent.

The first rushed forward. Black Bat countered his attack with her batons, kicked him in the groin and then elbowed him in the back of the head. The other two lunged at her, forcing her on the defensive, catching her off guard with their skill. Whomever was behind the abductions made sure the best fighters were protecting the targets.

Fortunately the batons where made of Wayne Tech material, allowing her to catch one sword at the cross section of her weapons and snapping it in two with a strong twist of her wrists. She followed that up by kicking the man so hard in the face his gas mask flew off, causing him to breath in the nerve agent. He passed out in seconds. The last one was about to jump her when Robin appeared behind him wearing a re-breather of his own and clubbed him in the back of the head with his sheathed straight-edged katana.

"Thanks." Cassandra said, looking around. "What happened?"

"The moment I attacked they released the gas. It seems they knew someone was going to show sooner or later. These guys were smart. From what I counted earlier two goons are missing. Probably the masterminds." Damian looked around the room. It was impossible to see how large it was due to the concealing smoke.

"Missing? The building is surrounded by the GCPD. They can't escape by walking out any of the doors. I saw no one use the stairs and the elevators aren't above this floor, which means..."

"The basement." Robin concluded. "They must have been digging a way out and didn't want to run the risk of someone breaking in and seeing it on the security footage. That would explain it."

"That's pretty paranoid." Black Bat remarked.

"This _is_ Gotham city, after all. Let's go get them." Damian began heading toward the elevators, with Cassandra right behind him.

"Robin," She began to say, "all the hostages are here except-"

"Cobblepot." Damian finished.

"Makes sense they would take him with them. He is worth the most money." Cassandra pointed out.

Robin said nothing as they hurried on.

Opening the automatic doors by hand revealed empty elevator shafts. Both masked heroes jumped on the support cables and slid their way down to the lowest floor where the elevator was. They entered through the maintenance hatch and, once inside, opened the doors.

To call it a basement was like calling a penthouse an attic. Just like the rest of the Lounge, it was expensively furnished, with dim lights, silk couches and chairs, more bars and casino game tables. The only thing that was out of place was the open, small secret entrance on the far northern wall. And sitting right next to the hole, bound with duct tape over his mouth, was Oswald Cobblepot.

The two vigilantes looked at the seemingly helpless man for a moment before Robin bent over and ripped the tape away with one hard pull.

"Arrgh!" The Penguin cried out, his face already turning red. "That hurt!"

"The words you are looking for are 'thank you'." Black Bat said coldly as Robin took a look in the man sized hole in the wall.

"For what? Showing up late?!" The short crime-lord scoffed. "All my guests have been traumatized and you punks get here after those yellow skinned Japs flew the coop! I hope the Big Man gets here because you two morons are completely incompetent!"

"This is your secret escape tunnel, isn't it?" Robin said, ignoring Oswald's abusive and racist rants. "There are subway rails, so I'm guessing a getaway car activated by voice and fingerprint scan."

Cobblepot seemed stunned by how quickly Robin put it altogether. "T-that's why they dragged me down here, to open the door and turn the car on for them. Don't know how they discovered it, seeing how I...silenced those who built it for me." Cobblepot struggled against the ropes that kept his hands behind his back.

Robin stared in silence at the man for a moment before he spoke.

"So, just to get this straight, these yakuza criminals crash your party, beat your trained security and held everyone for ransom. Then, when they sensed us coming, they released knockout gas to put everyone under, two of them came down here, dragged you along and forced you to open this secret door leading to a getaway car."

"That's right-" Oswald began.

But Robin wasn't finished. "And because they were in such a hurry to escape they took the time to tie and gag you again, because they would've had to free your hands and mouth in order for you to open this hidden door in the first place, right?"

Cobblepot fell silent.

"You over did it." Damian continued. "Took it one step too far."

Cassandra had a hard time keeping the surprise out of her voice, "You mean he-?"

"Staged the whole thing. He probably contacted the Yakuza himself and set up his guests to bleed them of money. He helped the leaders to escape otherwise they would've ratted him out if caught."

"But how can you be so sure?" Black Bat whispered so Cobblepot wouldn't hear.

"If you were in a rush to escape, would you waste time tying a hostage back up before you made your getaway?" Damian said quietly just before activating his earpiece, "Gordon."

" _Yeah?"_ Cassandra could hear the commissioner's voice over her own built-in headset.

"It's all clear. Be aware that the ground floor is flooded with knockout gas, so be sure to wear protection. The civilians might need medical attention. Cobblepot is in the basement."

" _Got it. Alright, all units, gear up and move in!"_

Cassandra watched as Robin turned off his earpiece and glared down at Penguin.

"You piece of trash!" He growled.

"N-now wait just a minute, boy!" The fat man began to protest.

"At least two people are dead tonight because of you! You're not happy enough running an illegal gambling ring along with drugs and prostitution, you need to get into the ransoming business too? What, did you want to get your hands on a new yacht?!"

"I-innocent! I'm innocent!" The Penguin yelled out in fear, though he had a glint of malice in his eyes.

"We've captured most of the men. Once I tell Gordon what you've done he'll put the pressure on during interrogation. You better start praying now that the Yakuza don't tell their men every single detail about their operations." Robin continued. "Because if they do, no amount of money will get you out of Black Gate this time."

"Sod off!" Cobblepot yelled.

Before Cassandra could react Robin drew out his katana from its sheath with a sharp ring and slashed at Oswald's stomach. The man let out yelp as his suit jacket and shirt burst open, revealing his bloated, pale skinned belly. Robin pressed his razor-sharp sword up against the Penguin's gut, a bead of blood forming at the point of contact.

"I have rights! You can't do this! You have no proof!" The man was yelling near hysterically.

"So what? Pull a stunt like this again, and I'll cut you open and stuff you like a turkey with your own dirty money, you understand me?!" Robin let the threat hang in the air for while.

"Robin..." Black Bat warned.

Penguin eyed the young hero, looking almost impressed. "Death threats? Even Batman doesn't take it that far."

"Who said I would kill you?" Robin gave the sword a twist, causing the blood to start dripping. Penguin cringed in pain. "It's amazing what the human body can endure. Come on, Black Bat. Let's go."

Sheathing his blade, Damian entered the secret entrance with Cassandra close behind, both disappearing in the dark leaving a sweaty, gasping Cobblepot behind. They both knew they couldn't prove he had been behind it all, and that he would soon enjoy millions upon millions of dollars more than he already had. It had made the night's victory bitter and unwanted. But it wasn't the first time they had experienced such a thing.

They followed the tracks until it led to one of many abandoned sewers in Gotham, running underneath the city like a mythical maze. They eventually found the getaway car; empty, of course. They could try tracking the men, but in the dirty waters beneath one of the filthiest cities in the world, it was next to impossible.

Cassandra could see Damian was greatly upset. Ever since she knew him the young man had pushed his mind and body to the impossible goal of being absolutely perfect to prove himself worth of Batman's trust, even if the Dark Knight had never asked for such a thing. They had just saved many lives, but Damian would only see how justice wasn't fully done, which angered him.

And that anger led him to do things she knew Batman would never approve of.

"Damian, I-" She began.

"Oh, dinner at the White Raven is at 9."

"What?" Cassandra asked, caught off guard.

"You agreed to have dinner with me, did you not?" Damian's voice had an undertone of authority to it, hinting that he wasn't really asking a question. "I made arrangements for our reservations to be moved to 9."

"I..." His sudden shift in attitude amazed the young Chinese woman. It was like a switch he could flip on and off. "I'll...have to change first."

"Of course. Alfred will pick you up from your hotel around 8:40. I'll see you shortly."

With that Damian turned down one particularly dark tunnel and vanished, leaving Cassandra alone. Maybe he wasn't as frustrated as she had believed.

* * *

 **Forgive any mistakes. If I was getting paid I'd still let some slip by.**

 **And now, for the part I've been really itching to get to...**


	4. Damian's Proposal

**Sorry for the huge leave of absence. Life is different now and so are my life goals. I still write, but it's harder to focus on side projects when I have much larger ones in the works. But you guys aren't here to listen to all that. So on with the show!**

 **Characters owned by DC, ruined by me. Enjoy.**

* * *

Damian's Proposal.

Gotham was known for its lavish things, and the restaurants were no exception. Cassandra Cain had at times wondered what eating a meal worth tens of thousands of dollars would taste like. The White Raven was Gotham's most expensive five star restaurant, making more money in a fiscal year than many small countries. And it was always full. So was it good? As it turned out the food was only as good as the company you kept, which was why everything tasted awkward.

Across the table from her, which was intimately small, sat Damian Wayne, inheritor to the multi-billion dollar Wayne Industry, current Robin, former ninja, and heir to the League of Shadows...if he so desired. It dawned on Cassie that if life had been just a little different, he might have ended up being her master and she would've been a potential bearer of his children. After all, that had been their parents' original plan.

At eighteen Damian alarmingly resembled his father, only more slender, youthful and with a far deadlier edge which could be seen in his blue eyes and whenever he grinned. Like Cassandra, this Wayne had been taught since birth to kill, and had spent the last several years resisting that tendency. And not always successfully.

Cassandra had to admit she had been surprised when the young Wayne contacted her through the back channels several days earlier, asking her if she would be willing to meet and talk. She accepted. However, the fancy restaurant and expensive set up wasn't what she had in mind.

"If the lobster is too cold, I can send for another one." Damian said around a mouthful of well-done Japanese beef. He still wasn't great on manners. "Or if you rather a table with a window view, I can arrange that too."

"No. No. Everything is fine." Cassandra ate a mouthful as if she needed to prove her words.

"~tt~" Damian sounded. "I expected you to be much better at lying than this."

"I have a tell?" Cassandra asked.

"No. I just know you better." Damian replied.

"A lucky guess." Cassandra countered.

"Grayson get's lucky...repeatedly. I'm just that good."

Ms. Cain rolled her eyes, ignoring how uncomfortable her backless dress was. Damian took a bite out of a roasted potato before speaking again.

"You did very well tonight." He said, referring to the earlier Iceberg Lounge incident.

"Nothing either one of us haven't done before." Cassandra took a sip of white wine.

"Efficient, strong, decisive, intelligent." Damian listed off all the qualities as though reading a list. "It makes what I'm about to ask next all the more...earnest."

Cassandra's training kicked in, her honed instincts and practiced body reading skills hitting her with such force she gave a start. The sudden call from Damian, his multiple compliments, his insistence on going to a over-priced and over-rated restaurant. This night wasn't about business, it was about pleasure.

"Hold on..." Cassandra almost gasped, keeping her voice hushed. "You want me to **date** you!?"

Damain's dangerous grin returned. " _Very_ intelligent. Though I had in mind something a little more...final."

Cassandra realized she had been thinking too small, to obvious. Damian wasn't speaking about courtship. That would take time and Damian's personality was practically built on being impatient. He was taking about _**marriage**_!

"Would _monsieur_ and _madame_ be vanting anything else?" The waiter suddenly intruded, his french accent more than just a little forced.

"Wine." Cassandra said, not breaking eye contact with Damian. "...A lot more wine."

They waited for the man to leave before continuing.

"Well?" Damian asked.

"Are you crazy?"

"Considering our 'day' jobs, more than likely..."

"What on earth would ever compel you to even consider this?" Cassandra asked with as low a voice as she could manage. The last thing she wanted was to make a scene.

Damian lowered his fork, put his elbows on the table and interlaced his fingers, looking at her very intensely.

"With father away for the foreseeable future I thought it would be best to have a partner to help with...what needs doing." The secret of remaining unknown vigilantes was to never talk about it in public and broad daylight. "Dick has his own responsibilities, Tim and Jason are out of the question. Steph and Babs are too...Steph and Babs. That left only you."

"But this goes a little beyond all that. You would never ask Grayson to..." Cassandra actually needed to pause to get in a steady breath before finishing her sentence. "...to marry you."

Damian held his gaze. "Yes...yes it does."

Silence.

Cassandra asked the next obvious question. "Why?"

"Have you had a single relationship since Bruce took you in? And I don't mean normal, social relationships. I am talking romantic. I bet that tonight is the closest you've ever come to a date in your entire life."

Cassandra realized Damian had no clue about Conner and decided not to bring it up. Besides, the boy of steel had been too good for her.

"And you think the kind of man I need is you?"

Damian shrugged. "Considering our backgrounds, I think we need each other."

Instinctively Cassandra understood what he was talking about. Shared life experience was a way for couples to bond, to understand one another. And who better to understand an assassin than another assassin? Not only that, but they had received almost identical training from the same organization.

"Look," Damian began to explain. "We're both brooding, emotionally stunted loners. Can you honestly say we would make great life partners with anyone remotely normal? I'm older now and I want an intimate relationship, but I don't want to be the kind of husband that makes her cry over and over again because I can't be sensitive enough for her. And I'm more than reasonably certain you would like to have a husband who doesn't always want you behaving like a blushing otaku school girl."

"That's...oddly specific." Cassandra noted. "But to make the leap from dating to making lifelong vows..."

"I've always been an admirer of animals that mate for life. There's a kind of nobility in it, an instinctual understanding that they will never betray one another. That's what I want to have." Damian explained.

"I recall the other 'proteges' tried this all well. None of them are still together." Cassandra remarked.

"But we're extremely self disciplined. Tim and Steph, Dick and Babs, they're amateurs compared to the iron will we have. I firmly believe we can show them how it's done." And then Damian said something that surprised Cassandra yet again. "I...I've never considered anyone else."

Cassandra stared back, eyes wide. "How long have you felt this way?"

"Not important." Damian said dismissively.

"Give me an answer." She insisted.

"Pretty much from the start." The young man admitted.

"Well...that explains...everything, I suppose." Cassandra said thoughtfully. "The cutting remarks, the sudden anger, always trying to outdo me at everything. All that was just-"

"A stupid teenage boy dealing with his first, huge crush." Damian admitted.

"You're still a teenager." Cassandra pointed-out.

"Is that a problem?"

"You think out of everything you've proposed that your age is the only problem? Damian, we hardly know each other. Not only that, but you yourself pointed out how different we are, that our upbringing has hardwired us to be unaffectionate killers, like monsters. You honestly think we could make this work?"

"Honestly? I think our odds are good." The young Wayne answered.

It felt like hours as Cassandra just sat there, looking at Damian from across the table, mulling everything over and over. There was merit to what Damian said. They were both highly trained, first by assassins and then by the world's greatest detective, with strong willpower and common goals.

"I can't believe I'm saying this, but... _if_ we do this, it's going to cause an uproar. Not only will we be dealing with living together as partners and lovers, but we will have to deal with the Family and everyone else we know. They will all tell us the same thing; that we're being reckless, foolish and idiotic. Because that's exactly what it would be."

"True." Damian admitted. "But I also think it's going to be a lot of fun."

Cassandra waited until the waiter brought the wine. She drank the entire bottle over the course of the next hour, then ordered another. Once that one was finished and she felt more than just a little light-headed, she gave her answer. "Very well...I accept."

Damian nodded, a grin on his face. It appeared to be one of excitement, but leaned more toward mischievous. He reached inside his pocket. "Then we'll do this as loudly as we can, for social media, of course. Ready?"

"You bought the ring already?" Cassandra asked, impressed at his confidence.

"You better believe I did. I'm a billionaire playboy's spoiled rotten son about to asked his ditzy girlfriend to make the biggest mistake of her life. You think I'd miss the chance to do this at the most highbrow restaurant in Gotham? Don't forget to be in character."

Damian's face suddenly changed into one that Cassandra recognized as a false persona. Bruce would use one whenever he faced the media and large social gathering. It seemed Damian had perfected his own. Face seemingly red with wine, Damian rose up from the table, walked around it until he was standing right in front of her, revealed a small box in the palm of his hand and knelt down on one knee, eyes bright with worry and expectant hope.

"Cassie." He said loudly enough for those near by to hear him. "Will you marry me?"

Cassandra, who could slow her heartbeat till it could be read as a flat-line, was certainly able to conjure up some crocodile tears, place her hand over her mouth and squeal with delight. "EEEEEE! Oh Damian!Yes! Yes I will!"

As she leapt into his arms and they began to do what could be best described as typical young people lip mashing, the rest of the restaurant guests, their meals now interrupted, broke out into polite applause.

Despite the acting, deep in the back of her mind, Cassandra Cain found herself enjoying her very first kiss with Damian Wayne...

* * *

 **I must've written 8 different versions of this scene. Everything hinges on this one idea that Damian can convince Cassandra to do this one thing that is pretty much absurd. I'm still not convinced I got it right, so I understand if this is where you decide to get off. For those of you still around, I'll try to get the next chapter up before too long. I hope...  
**


End file.
